[ CAS No. 32249-35-7 ] {[proInfo.proName]}

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2D 3D

Structure of 32249-35-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 32249-35-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 32249-35-7 ]

SDS Specification

Alternatived Products of [ 32249-35-7 ]

Product Details of [ 32249-35-7 ]

CAS No. :	32249-35-7	MDL No. :	MFCD00274090
Formula :	C₇H₁₀O₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	RIJWDPRXCXJDPK-UHFFFAOYSA-N
M.W :	142.15	Pubchem ID :	10130016
Synonyms :		Chemical Name :	Methyl 3-cyclopropyl-3-oxopropanoate

Calculated chemistry of [ 32249-35-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.71
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	35.13
TPSA :	43.37 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.44
Log Po/w (XLOGP3) :	0.43
Log Po/w (WLOGP) :	0.47
Log Po/w (MLOGP) :	0.25
Log Po/w (SILICOS-IT) :	1.13
Consensus Log Po/w :	0.74

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.73
Solubility :	26.6 mg/ml ; 0.187 mol/l
Class :	Very soluble
Log S (Ali) :	-0.91
Solubility :	17.6 mg/ml ; 0.124 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.88
Solubility :	18.6 mg/ml ; 0.131 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.59

Safety of [ 32249-35-7 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 32249-35-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 32249-35-7 ]
Downstream synthetic route of [ 32249-35-7 ]

[ 32249-35-7 ] Synthesis Path-Upstream 1~2

1
[ 32249-35-7 ]
[ 586966-54-3 ]

Reference： [1] Patent: US2012/16129, 2012, A1,
[2] Patent: US2012/16129, 2012, A1,

2
[ 32249-35-7 ]
[ 862695-75-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6756 - 6761

[ 32249-35-7 ] Synthesis Path-Downstream 1~5

1
[ 6294-89-9 ]
[ 32249-35-7 ]
[ 183303-75-5 ]

Yield	Reaction Conditions	Operation in experiment
70%		Production of methyl 4-cyclopropyl-1,2,3-thiadiazole-5-carboxylate Methyl 3-cyclopropyl-3-oxopropionate (10 g; 70 mmols) was dissolved in methanol (100 ml), and methyl carbazinate (6.3 g; 70 mmols) and p-toluenesulfonic acid (20 mg; 0.11 mol) were added thereto. After stirring the mixture overnight, methanol was evaporated under reduced pressure. Subsequently, toluene (10 ml) was added thereto, and thionyl chloride (20 ml) was gradually added dropwise thereto under cooling in an ice-bath. After completion of the dropwise addition, the mixture was stirred for 4 hours at room temperature, then poured onto ice to stop the reaction, and neutralized with sodium hydrogencarbonate. After extracting with ethyl acetate and washing with a saturated sodium chloride aqueous solution, the solution was dried over anhydrous sodium sulfate. After the mixture was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 10:1) to thereby obtain 9 g of methyl 4-cyclopropyl-1,2,3-thiadiazole-5-carboxylate. Yield: 70% Physical properties: mp. 47C

Reference： [1]Patent: EP1852428,2007,A1 .Location in patent: Page/Page column 31-32

2
[ 32249-35-7 ]
[ 4637-24-5 ]
[ 124845-04-1 ]

Yield	Reaction Conditions	Operation in experiment
80.13%		1,1-Dimethoxy-N,N-dimethylmethanamine (1, 24g, 0.2 mol) andmethyl 3-cyclopropyl-3-oxo- propanoate (2, 28g, 0.2 mol) weremixed and heated for 20 h at 60 C. The obtained yellow oil wasfirstly dissolved in methanol (200 mL) and water (100 mL), andthen hydroxylamine hydrochloride (14g, 0.2 mol) was added. Thesolvents were evaporated under vacuum after the mixture washeated for 90 min at 60 C. The residuewas dissolved in the mixtureof acetic acid (100 mL) and concentrated HCl (100 mL) and refluxedfor 4h. The reaction mixture was diluted with water (500 mL) and extracted with ethyl acetate (200 mL 3). The organic layer wascombined and washed with brine, and then dried with anhydroussodium sulfate. Ethyl acetate was evaporated under vacuum. Theresidue was subjected to a silica gel column and eluted with themixture of ethyl acetate and petroleum ether at the ratio of 1:3 (v/v) to afford 3. Compound 3 was obtained as white solid (yield80.13%), mp, 163e165 C; 1H NMR (500 MHz, Chloroform-d): d 8.53(s, 1H), 2.91 (m, 1H), 1.38 (m, 2H), 1.3 (m, 2H). 13C NMR (126 MHz,Chloroform-d): d 179.91, 167.63, 150.62, 108.36, 10.86, 8.87. ESI-MS:m/z 152, [M H]-.
		Methyl 3-cyclopropyl-3-oxopropanoate (0.28 g, 2 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (0.24 g, 2 mmol) was mixed and heated for 20 h at 60 C. The bright yellow oil was dissolved in methanol (2 mL) and H2O (1 mL) and hydroxylamine hydrochloride (0.14 g, 2 mmol) was added, resulting in a pH of ca 5. The reaction was heated for 90 min at 60 C. The solvents were evaporated and the residue refluxed in acetic acid: conc. HCl (3+3 mL) for 4 h. The mixture was stored at room temperature for 2 days and the solid was filtered off and dried in vacuum to yield the title compound as a grey solid. This compound is also commercially available. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.18-1.28 (m, 2H) 1.28-1.35 (m, 2H) 2.78-2.90 (m, 1H) 8.45 (s, 1H)

Reference： [1]Journal of Molecular Structure,2020,vol. 1220
[2]Patent: US2008/21022,2008,A1 .Location in patent: Page/Page column 96
[3]Journal of Agricultural and Food Chemistry,2020,vol. 68,p. 15107 - 15114

3
[ 32249-35-7 ]
[ 862695-75-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6756 - 6761

4
[ 23687-26-5 ]
[ 32249-35-7 ]
3-cyclopropyl-N-(isoquinolin-6-yl)-3-oxopropanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
880 mg	at 100℃;	6-Aminoisoquinoline (1.0 g, 6.94 mmol) was heated in methyl 3-cyclopropyl-3-oxopropanoate (5 mL) at 100° C. overnight. The reaction mixture was cooled to RT then applied to a pad of silica and washed with DCM then eluted using 5percent methanol in DCM. This fraction was evaporated and the resultant crude product was chromatographed on a 100 g Si cartridge eluting with 0-5percent methanol in DCM. The product was obtained as a brown oil (880 mg). LCMS (Method 6): Rt=0.67 min, m/z 255.1 [M+H]+

Reference： [1]Patent: US2018/170939,2018,A1 .Location in patent: Paragraph 0423-0425

5
[ 120-72-9 ]
[ 32249-35-7 ]
[ 621-63-6 ]
methyl 2-cyclopropyl-4-(1H-indol-3-yl)-4,5-dihydrofuran-3-carboxylate [ No CAS ]

Reference： [1]Green Chemistry,2019,vol. 21,p. 2061 - 2069

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Isomers

Technical Information

? Acyl Group Substitution ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bouveault-Blanc Reduction ? Bucherer-Bergs Reaction ? Catalytic Hydrogenation ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Ester Cleavage ? Fischer Indole Synthesis ? Grignard Reaction ? Halogenation ? Heat of Combustion ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

Pharmaceutical Intermediates of
[ 32249-35-7 ]

Pitavastatin Related Intermediates

[ 147489-06-3 ]

t-Butyl (3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-isopropylidenedioxy-6-heptenoate

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[ 32249-35-7 ]

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Ethyl 3-cyclopropyl-3-oxopropanoate

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Methyl 4-methyl-3-oxopentanoate

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Ethyl 3-cyclopropyl-3-oxopropanoate

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P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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[ CAS No. 32249-35-7 ] {[proInfo.proName]}

Quality Control of [ 32249-35-7 ]

Related Doc. of [ 32249-35-7 ]

Product Details of [ 32249-35-7 ]

Calculated chemistry of [ 32249-35-7 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 32249-35-7 ]

Application In Synthesis of [ 32249-35-7 ]

[ 32249-35-7 ] Synthesis Path-Upstream 1~2

[ 32249-35-7 ] Synthesis Path-Downstream 1~5

Technical Information

Pharmaceutical Intermediates of [ 32249-35-7 ]

Pitavastatin Related Intermediates

Related Functional Groups of [ 32249-35-7 ]

Aliphatic Cyclic Hydrocarbons

Esters

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Pharmaceutical Intermediates of
[ 32249-35-7 ]

Related Functional Groups of
[ 32249-35-7 ]